Electric Literature of 1117-71-1,Some common heterocyclic compound, 1117-71-1, name is Methyl 4-bromobut-2-enoate, molecular formula is C5H7BrO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
A suspension of sodium acetate (3.5 g, 42 mmol) in MeCN (30 ml.) was treated with methyl 4-bromocrotonate (Aldrich) (3.33 ml_, 5 g, 28 mmol) and the mixture was heated to 50 C for 3 d. The mixture was diluted with ether and then filtered. The solid was washed with ether and the combined filtrate and washings was evaporated under reduced pressure. After evaporation the residue was partitioned between ether and water. The organic phase was washed with aqueous sodium bicarbonate, dried over MgSCM, and evaporated under reduced pressure to give a pale orange oil. NMR indicated a mixture of product and starting material, therefore, sodium acetate (3.44 g, 42 mmol) was added to the residual oil, followed by MeCN (10 ml.) and the mixture was heated to 70 C over the weekend. The mixture was concentrated under reduced pressure and the residue was partitioned between ether and water. The organic solution was washed with water, brine, dried (MgSCM) and filtered. The filtrate was evaporated under reduced pressure to give the title compound (3.55 g, 80%) as an orange oil: NMR delta (CDC ) 6.92 (dt, J 16, 5 Etazeta,IotaEta), 6.01 (dt, J 16, 2 Hz, 1H), 4.72 (dd, J 5, 2 Hz, 2H), 3.73 (s, 3H), 2.10 (s, 3H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-bromobut-2-enoate, its application will become more common.
Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BARRETT, Tim; HATLEY, Richard Jonathan Daniel; MACDONALD, Simon John Fawcett; SAKLATVALA, Paula; TSE, Sing Yuen Eric; (35 pag.)WO2017/158072; (2017); A1;,
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